The Pilot Money Guys

What if most individual stocks actually don't outperform and a small handful of massive winners are doing all the heavy lifting? In this episode, renowned finance professor Hank Bessembinder joins the show to break down...

What if we're asking the wrong question about market peaks, bubbles, and crashes? Everyone wants to know what happens next, but this episode shifts the focus to what you can actually control: risk, timing, and smart...

What happens when success, identity, and purpose collide with some of the hardest battles a person can face? In this powerful conversation with Ryan Watson, we explore the realities many pilots and high-performing...

Are private equity and alternative investments really the secret weapon of the wealthy or are public markets still your best bet? In this episode, we tackle one of the most common questions we hear: should you look...

Why do airlines struggle to make money even when planes are full? In this episode, we unpack the surprising economics behind one of the world's most essential yet fragile industries. From razor-thin profit margins to...

What do the new Secure Act 2.0 rules mean for Roth contributions and retirement planning in 2025? In this episode, we explore what pilots and high-income earners need to know about Roth catch-up contributions, required...

What actually makes for a happy, fulfilling retirement? Is it all about the numbers, or is there more to the story? In this episode, Dr. Michael Finke—professor, researcher, and one of the most respected voices in...

What exactly is private equity, and why is it suddenly being linked to your 401(k)? In this episode, we break down the recent executive order that directs the Department of Labor to explore ways of including private...

How can you avoid running out of money in retirement and still live the life you want? In this episode, we break down the most important strategies for sustainable retirement spending. You'll learn how retirement...

Is Social Security really running out of money, or is that just a headline meant to scare you? In this episode, we cut through the noise to uncover the truth about its future, its viability, and how it actually works...

Are you wondering what the sweeping changes brought by the recently passed "One Big Beautiful Bill Act" (OBBBA) are? In this episode, we break down the new legislation, providing a clear overview of how it impacts...

What do you do when your aging parent needs care, but you live across the country and don't know where to start? In this episode, Casey Rausin, RN, CCM, and CEO of HOMECAREceo Forum, joins the show to help answer that...

Is Medicare more confusing than it should be? If you're nearing retirement or thinking about leaving your job early, the healthcare piece can feel overwhelming and expensive. In this episode, we sit down with Cole...

Does the phrase "long-term care" make you cringe? If so, you're not alone, but it's something we all need to think about eventually. In this episode, we sit down with Amy Arnett, VP of Insurance Solutions at DPL...

What is a Market-Based Cash Balance Plan (MBCBP), and why is it becoming the go-to retirement vehicle for pilots at major airlines like Delta? In this episode, we explain what an MBCBP actually is, how it's different...

Can a mindset of gratitude really change your financial life? In this episode, we explore how the power of gratitude directly influences your outlook, your decisions, and ultimately, your financial success. You'll learn...

What if you're about to retire—and the market takes a nosedive? For those in their 60s, looking toward retirement at 65, market volatility can feel like a punch to the gut. In this episode, we dive into how to...

What do you do when the world feels unpredictable—and your financial future even more so? In this episode, we're diving into how pilots can mentally and financially prepare for uncertain times. From industry shake-ups...

What good is wealth if you don't feel good? For busy professionals—especially pilots—maintaining health and nutrition while constantly on the go is a major challenge. In this episode, financial planner Mark Covell and...

Is direct indexing the right investment strategy for you? In this episode, Shawn Jaberzadeh, Co-Head of Enterprise Group at Dimensional Fund Advisors, breaks down how direct indexing works and when it might be a better...

How can you teach your kids smart money habits without creating entitlement? In this episode, we dive into the essential lessons of raising financially responsible children. We explore the challenges first-generation...

What does it take to transition from a TOPGUN fighter pilot to a bestselling author? Jack Stewart, a former U.S. Navy fighter pilot with 23 years of service, joins the show to share his fascinating journey from flying...

What does it take to redefine success and find joy in the journey, not just the results? In this episode, we're joined by Anthony Thompson, CEO of Thompson Consulting & Advising, a mindset and performance coach, and...

Are you a young professional pilot looking to build a solid financial foundation? In this episode, we sit down with Lisa Rosenthal, COO, Nolan Clark, Associate Financial Planner, and Jon Schultz, Paraplanner, to discuss...

Is the market overvalued and on the brink of an implosion? Join us as we dive into the intricacies of market valuation and investment strategies. In this replay episode, we're tackling some of the pressing questions...